GB1364140A - 1-carbamoyl-benzimidazoles processes for their production and their fungicidal and bactericidal use - Google Patents
1-carbamoyl-benzimidazoles processes for their production and their fungicidal and bactericidal useInfo
- Publication number
- GB1364140A GB1364140A GB4208672A GB4208672A GB1364140A GB 1364140 A GB1364140 A GB 1364140A GB 4208672 A GB4208672 A GB 4208672A GB 4208672 A GB4208672 A GB 4208672A GB 1364140 A GB1364140 A GB 1364140A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl
- carbamic acid
- carbamoyl
- fungicidal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- JZRIIAYLOPWOHN-UHFFFAOYSA-N benzimidazole-1-carboxamide Chemical class C1=CC=C2N(C(=O)N)C=NC2=C1 JZRIIAYLOPWOHN-UHFFFAOYSA-N 0.000 title abstract 3
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
- 230000000855 fungicidal effect Effects 0.000 title abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- ADIHOOMDBWOIPW-UHFFFAOYSA-N (1-carbonochloridoylbenzimidazol-2-yl)carbamic acid Chemical compound C1=CC=C2N(C(Cl)=O)C(NC(=O)O)=NC2=C1 ADIHOOMDBWOIPW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical compound C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 abstract 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Abstract
1364140 1 - carbamoylbenzimidazole derivatives BAYER AG 11 Sept 1972 [11 Sept 1971] 42086/72 Heading C2C Novel 1 - carbamoyl - benzimidazole derivatives having the general formula or of the tantomeric formula wherein R<SP>1</SP> is (C 1 -C 4 ) alkyl or alkenyl and R<SP>2</SP> is a group of the formula or -(CH 2 )n-S-CO.R<SP>6</SP>; R<SP>3</SP> is hydrogen or (C 1 -C 6 ) alkyl; R<SP>4</SP> and R<SP>5</SP> are hydrogen or (C 1 -C 4 ) alkyl; R<SP>6</SP> is (C 1 -C 4 ) alkyl or alkenyl or a phenyl group optionally substituted by one or more of halogen, nitro, nitrile and/or (C 1 -C 4 ) alkyl and alkoxy; X is halogen, nitro, nitrile, and/or (C 1 -C 4 ) alkyl or alkoxy; m is 1-12, n is 2 or 3 and p is 0-5, are prepared by either (a) reacting a benzimidazol-2-yl carbamic acid ester of the general formula with an isocyanate of the formula OCN-R<SP>2</SP>, or with a carbamic acid chloride of the formula Cl.CO.NHR<SP>2</SP>, or (b) reacting a 1-(chlorocarbonyl) - benzimidazol - 2 - yl carbamic acid ester of the formula with an amine of the formula NH 2 .R<SP>2</SP>. The reaction is preferably carried out at a temperature of from 0 to 30 C. in an inert organic solvent. The novel compounds possess fungicidal and bactericidal properties.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2145512A DE2145512A1 (en) | 1971-09-11 | 1971-09-11 | 1-CARBAMOYL BENZIMIDAZOLE, METHOD OF MANUFACTURING IT, AND USE OF FUNGICIDES AND BACTERICIDES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1364140A true GB1364140A (en) | 1974-08-21 |
Family
ID=5819294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4208672A Expired GB1364140A (en) | 1971-09-11 | 1972-09-11 | 1-carbamoyl-benzimidazoles processes for their production and their fungicidal and bactericidal use |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3903102A (en) |
| JP (2) | JPS4836172A (en) |
| BE (1) | BE788637A (en) |
| BR (1) | BR7206268D0 (en) |
| DE (1) | DE2145512A1 (en) |
| FR (1) | FR2152255A5 (en) |
| GB (1) | GB1364140A (en) |
| IL (1) | IL40326A0 (en) |
| IT (1) | IT967323B (en) |
| NL (1) | NL7212253A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59112001A (en) * | 1982-12-13 | 1984-06-28 | 高木 正一 | Panty |
| JPS6130008U (en) * | 1984-07-26 | 1986-02-22 | 株式会社 菊水商会 | shorts |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1936130A1 (en) * | 1969-07-16 | 1971-01-28 | Bayer Ag | Benzimidazole derivatives, process for their preparation and their fungicidal use |
| DE2044205A1 (en) * | 1970-09-07 | 1972-03-16 | Farbwerke Hoechst AG, vorm Meister Lucius & Bruning, 6000 Frankfurt | New Benzimidazoles |
| US3738995A (en) * | 1971-05-14 | 1973-06-12 | Du Pont | Solvent process for the preparation of 1 - carbamoyl-substituted 2 - benzimidazolecarbamates |
-
0
- BE BE788637D patent/BE788637A/en unknown
-
1971
- 1971-09-11 DE DE2145512A patent/DE2145512A1/en active Pending
-
1972
- 1972-09-05 US US286534A patent/US3903102A/en not_active Expired - Lifetime
- 1972-09-08 IL IL40326A patent/IL40326A0/en unknown
- 1972-09-08 NL NL7212253A patent/NL7212253A/xx unknown
- 1972-09-09 IT IT29027/72A patent/IT967323B/en active
- 1972-09-11 GB GB4208672A patent/GB1364140A/en not_active Expired
- 1972-09-11 JP JP47090490A patent/JPS4836172A/ja active Pending
- 1972-09-11 FR FR7232103A patent/FR2152255A5/fr not_active Expired
- 1972-09-11 BR BR006268/72A patent/BR7206268D0/en unknown
- 1972-09-11 JP JP47090491A patent/JPS4836339A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE788637A (en) | 1973-03-12 |
| IL40326A0 (en) | 1972-11-28 |
| NL7212253A (en) | 1973-03-13 |
| JPS4836339A (en) | 1973-05-29 |
| JPS4836172A (en) | 1973-05-28 |
| US3903102A (en) | 1975-09-02 |
| IT967323B (en) | 1974-02-28 |
| BR7206268D0 (en) | 1973-08-23 |
| FR2152255A5 (en) | 1973-04-20 |
| DE2145512A1 (en) | 1973-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |